Synthesis, spectral characterization and electrochemical properties of (2-alkylthiobenzoyl)ferrocenes. Crystal structures of 2-methylthio, 2-ethylthio and 2-isopropylthio derivatives
Само за регистроване кориснике
2010
Аутори
Ratkovic, ZoranNovaković, Slađana B.
Bogdanović, Goran A.
Šegan, Dejan M.
Vukicevic, Rastko D.
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
The one-pot synthesis of seven new (2-alkylthiobenzoyl)ferrocenes has been achieved by Friedel-Crafts acylation of ferrocene with acid chlorides generated in situ from the corresponding carboxylic acids and phosphorous trichloride. The obtained compounds were characterized by spectroscopic data (UV, IR, (1)H and (13)C NMR), whereas their electrochemical properties have been investigated by cyclic voltammetry. The single-crystal X-ray structure determinations for three of them are also reported. Each of the three derivatives exhibits the intramolecular C-H center dot center dot center dot O interaction which involves the donor from the cyclopentadienyl (Cp) ring and the carbonyl oxygen as acceptor. This interaction favors the coplanar arrangement of the two moieties. The angles between the vectors coinciding the C-O bonds and the corresponding Cp planes are all below 6.4 degrees. Conventional hydrogen bonds do not exist in any of the three crystal structures but some weak intermolecular... interactions of the C-H center dot center dot center dot, C-H center dot center dot center dot S and C-H center dot center dot center dot pi types have been found and analyzed in detail. Different geometrical parameters for these crystal structures as well as for 22 similar ones extracted from Cambridge Structural Database (CSD) have been compared and analyzed. (C) 2010 Elsevier Ltd. All rights reserved.
Кључне речи:
Ferrocene / 2-Alkylthiobenzoic acids / (2-Alkylthiobenzoyl)ferrocenes / Cyclic voltammetry / Crystal structure / C-H center dot center dot center dot pi interactionsИзвор:
Polyhedron, 2010, 29, 11, 2311-2317Издавач:
- Pergamon-Elsevier Science Ltd, Oxford
Финансирање / пројекти:
- Развој нових електрохемијских и хемијских метода органске синтезе (RS-MESTD-MPN2006-2010-142042)
- Синтеза, карактеризација и активност органских и координационих једињења и њихова примена у (био)нанотехнологији (RS-MESTD-MPN2006-2010-142010)
DOI: 10.1016/j.poly.2010.04.034
ISSN: 0277-5387
WoS: 000280634300011
Scopus: 2-s2.0-77954621246
Колекције
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Ratkovic, Zoran AU - Novaković, Slađana B. AU - Bogdanović, Goran A. AU - Šegan, Dejan M. AU - Vukicevic, Rastko D. PY - 2010 UR - https://cherry.chem.bg.ac.rs/handle/123456789/1098 AB - The one-pot synthesis of seven new (2-alkylthiobenzoyl)ferrocenes has been achieved by Friedel-Crafts acylation of ferrocene with acid chlorides generated in situ from the corresponding carboxylic acids and phosphorous trichloride. The obtained compounds were characterized by spectroscopic data (UV, IR, (1)H and (13)C NMR), whereas their electrochemical properties have been investigated by cyclic voltammetry. The single-crystal X-ray structure determinations for three of them are also reported. Each of the three derivatives exhibits the intramolecular C-H center dot center dot center dot O interaction which involves the donor from the cyclopentadienyl (Cp) ring and the carbonyl oxygen as acceptor. This interaction favors the coplanar arrangement of the two moieties. The angles between the vectors coinciding the C-O bonds and the corresponding Cp planes are all below 6.4 degrees. Conventional hydrogen bonds do not exist in any of the three crystal structures but some weak intermolecular interactions of the C-H center dot center dot center dot, C-H center dot center dot center dot S and C-H center dot center dot center dot pi types have been found and analyzed in detail. Different geometrical parameters for these crystal structures as well as for 22 similar ones extracted from Cambridge Structural Database (CSD) have been compared and analyzed. (C) 2010 Elsevier Ltd. All rights reserved. PB - Pergamon-Elsevier Science Ltd, Oxford T2 - Polyhedron T1 - Synthesis, spectral characterization and electrochemical properties of (2-alkylthiobenzoyl)ferrocenes. Crystal structures of 2-methylthio, 2-ethylthio and 2-isopropylthio derivatives VL - 29 IS - 11 SP - 2311 EP - 2317 DO - 10.1016/j.poly.2010.04.034 ER -
@article{ author = "Ratkovic, Zoran and Novaković, Slađana B. and Bogdanović, Goran A. and Šegan, Dejan M. and Vukicevic, Rastko D.", year = "2010", abstract = "The one-pot synthesis of seven new (2-alkylthiobenzoyl)ferrocenes has been achieved by Friedel-Crafts acylation of ferrocene with acid chlorides generated in situ from the corresponding carboxylic acids and phosphorous trichloride. The obtained compounds were characterized by spectroscopic data (UV, IR, (1)H and (13)C NMR), whereas their electrochemical properties have been investigated by cyclic voltammetry. The single-crystal X-ray structure determinations for three of them are also reported. Each of the three derivatives exhibits the intramolecular C-H center dot center dot center dot O interaction which involves the donor from the cyclopentadienyl (Cp) ring and the carbonyl oxygen as acceptor. This interaction favors the coplanar arrangement of the two moieties. The angles between the vectors coinciding the C-O bonds and the corresponding Cp planes are all below 6.4 degrees. Conventional hydrogen bonds do not exist in any of the three crystal structures but some weak intermolecular interactions of the C-H center dot center dot center dot, C-H center dot center dot center dot S and C-H center dot center dot center dot pi types have been found and analyzed in detail. Different geometrical parameters for these crystal structures as well as for 22 similar ones extracted from Cambridge Structural Database (CSD) have been compared and analyzed. (C) 2010 Elsevier Ltd. All rights reserved.", publisher = "Pergamon-Elsevier Science Ltd, Oxford", journal = "Polyhedron", title = "Synthesis, spectral characterization and electrochemical properties of (2-alkylthiobenzoyl)ferrocenes. Crystal structures of 2-methylthio, 2-ethylthio and 2-isopropylthio derivatives", volume = "29", number = "11", pages = "2311-2317", doi = "10.1016/j.poly.2010.04.034" }
Ratkovic, Z., Novaković, S. B., Bogdanović, G. A., Šegan, D. M.,& Vukicevic, R. D.. (2010). Synthesis, spectral characterization and electrochemical properties of (2-alkylthiobenzoyl)ferrocenes. Crystal structures of 2-methylthio, 2-ethylthio and 2-isopropylthio derivatives. in Polyhedron Pergamon-Elsevier Science Ltd, Oxford., 29(11), 2311-2317. https://doi.org/10.1016/j.poly.2010.04.034
Ratkovic Z, Novaković SB, Bogdanović GA, Šegan DM, Vukicevic RD. Synthesis, spectral characterization and electrochemical properties of (2-alkylthiobenzoyl)ferrocenes. Crystal structures of 2-methylthio, 2-ethylthio and 2-isopropylthio derivatives. in Polyhedron. 2010;29(11):2311-2317. doi:10.1016/j.poly.2010.04.034 .
Ratkovic, Zoran, Novaković, Slađana B., Bogdanović, Goran A., Šegan, Dejan M., Vukicevic, Rastko D., "Synthesis, spectral characterization and electrochemical properties of (2-alkylthiobenzoyl)ferrocenes. Crystal structures of 2-methylthio, 2-ethylthio and 2-isopropylthio derivatives" in Polyhedron, 29, no. 11 (2010):2311-2317, https://doi.org/10.1016/j.poly.2010.04.034 . .